Limited research has been conducted into the teaching primary principalship in Australia, as the focus has tended to be on full time school principals. It has often been assumed that principalship role in smaller primary schools is a 'scaled down' version of a full time primary principalship and that similar leadership and management approaches apply. There is limited recognition of the unique challenges of teaching primary principals who have the dual roles of school management and classroom teaching responsibilities in devolving school systems. A mixed method research design was developed to explore the current issues, challenges and concerns of teaching primary principals in three school systems in New South Wales. In-depth interviews with teaching primary principals informed the development of a survey which was forwarded to Department of Education and Training, Catholic and Seventh-day Adventist teaching primary principals in New South Wales. The paper explores results of the qualitative aspects of the research design which indicate that teaching primary principals are experiencing work intensification and increased role complexity conflict resulting in guilt and frustration as they endeavour to cope with the dual roles of teaching and administration. Issues of adequate administration release time, isolation, professional preparation and support, capacity for instructional leadership, and career advancement are compared across school systems.